Numerous types of head support systems are known and may be used to assist in supporting the head of a user while seated, for example, while sleeping on aircraft, buses, and the like. Unfortunately, many such systems work better in theory than in practice. For example, many head support systems involve the use of straps, tethers, and lanyards that are not only difficult and cumbersome to set up and adjust but also quite obvious in use and indiscrete. Furthermore, once set up and adjusted, many such systems do not permit the user to easily disengage and re-engage the support system, such as required if the user decides to subsequently leave the seat for a short period of time. While other systems have been developed that do not require the use of straps or lanyards, they typically require specialized fixtures or components that are also difficult to use and often not comfortable for the user. As a consequence, such prior art head support systems have never enjoyed widespread use and consumer acceptance.